Ethyl Acetate → HCID 131709940, compound

HRID 1580503Notes

Reaction equation

HRID 1580503 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:32][C:8]([CH2:9][C:10]2[CH:15]([C:16]([OH:18])=[O:17])[N:14]3[C:19](=[O:30])[C@@H:20]([C:21](=[O:29])[CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C@H:13]3[S:12][C:11]=2[NH2:31])=[CH:7][CH:6]=1)=[O:4].C(O[CH2:37][CH3:38])(=O)C>CO>[C:23]1([CH:22]([O:17][C:16]([CH:15]2[N:14]3[C:19](=[O:30])[C@@H:20]([C:21](=[O:29])[CH2:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C@H:13]3[S:12][C:11]([NH2:31])=[C:10]2[CH2:9][C:8]2[O:32][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[O:18])[C:38]2[CH:37]=[CH:3][CH:5]=[CH:6][CH:7]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 131709941HCID 131709941, compound

Product 1

HCID 131709940HCID 131709940, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6.85 g of crystallised 3-(5-methoxycarbonyl-furfuryl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid in 50 ml of methanol is treated with 100 ml of ethyl acetate and the methanol is almost completely removed under reduced pressure. A total of 6.0 g of crude diphenyldiazomethane is then added in small amounts. The reaction mixture is freed from solvent after a total reaction period of 60 minutes at room temperature. The residual oil is triturated with 500 ml of petroleum ether, the undissolved material is filtered off and crystallised from 100 ml of hot ethyl acetate. The first crystalline fraction is recrystallised twice from a mixture of methylene chloride and cyclohexane to yield the 3-(5-methoxycarbonyl-furfuryl)-7β-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid diphenylmethyl ester in the form of colourless felted needles, m.p. 164°-166°; [α]D20 = + 267° ± 1° (c = 1.134 in chloroform): thin-layer chromatogram (silica gel): Rf = 0.71 (system: toluene/ethyl acetate 1:1), Rf = 0.60 (system: toluene/ethyl acetate 2:1), Rf = 0.70 (system: toluene/acetone 2:1), Rf = 0.49 (system: toluene/acetone 4:1) and Rf = 0.30 (system toluene/acetone 9:1); ultraviolet absorption spectrum (in 95% ethanol): λmax = 268 mμ (ε = 21000) and λmin = 234 mμ (ε = 11000); infrared absorption spectrum (in mineral oil): characteristic bands at 2,98μ, 5,61μ, 5,74μ, 6,03μ, 6,53μ, 7,59μ, 8,26μ, 8,54μ, 8,72μ, 9,81μ, 10,14μ, 13,13μ and 14,42μ.

Workup

  1. customthe methanol is almost completely removed under reduced pressure
  2. additionA total of 6.0 g of crude diphenyldiazomethane is then added in small amounts
  3. customafter a total reaction period of 60 minutes at room temperature
  4. customThe residual oil is triturated with 500 ml of petroleum ether
  5. filtrationthe undissolved material is filtered off
  6. customcrystallised from 100 ml of hot ethyl acetate
  7. customThe first crystalline fraction is recrystallised twice from a mixture of methylene chloride and cyclohexane

Sources & evidence

ORD record
ord-7bc3bb91605c4b7ea91085805c1342e5
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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